Ethyl isocyanate → 1-(5-Bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea

HRID 1399976Notes

Reaction equation

HRID 1399976 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>O1CCOCC1>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[S:9][C:8]([NH:10][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 596030945-Bromo-6-fluorobenzo[d]thiazol-2-amine

Product 1

HCID 596030721-(5-Bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-ureaYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of iii (0.36 g, 1.45 mmol) in 1,4-dioxane (25.0 mL) was added ethyl isocyanate (0.69 mL, 8.74 mmol) and the mixture heated at 80° C. for 15 h. The solvent was evaporated and the residue stirred with H2O at 60° C. for 5 h. The solution was filtered and washed with Et2O to obtain Intermediate 13 (0.30 g, 69%).

Workup

  1. customThe solvent was evaporated
  2. filtrationThe solution was filtered
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-ee6883bf1baf4384814f41a0a8a88e92
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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